Umbelliferone → 7-[2-(N-Dodecyl-N-methylamino)ethoxy]-2H-1-benzopyran-2-one

HRID 1700879Notes

Reaction equation

[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:12])[O:9]2)=[CH:4][CH:3]=1.[CH2:13]([N:25]([CH2:27][CH2:28]O)[CH3:26])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>>[CH2:13]([N:25]([CH2:27][CH2:28][O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:6]=[CH:7][C:8](=[O:12])[O:9][C:10]=2[CH:11]=1)[CH3:26])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

Reactant 2

HCID 5281426Umbelliferone

HCID 10657884Dodecyl(2-hydroxyethyl)methylamine

Product 1

HCID 183190607-[2-(N-Dodecyl-N-methylamino)ethoxy]-2H-1-benzopyran-2-oneYield 47%

Procedure

7-Hydroxycoumarin (6.0 g, 37.0 mmol) and 2-[N-dodecyl-N-methylamino] ethanol (9.0 g, 37.0 mmol) were reacted by the general procedure as described in example 1 and afforded the title compound (6.7 g, 47%) as a white solid.

Sources & evidence

ORD record: ord-2316d118d6e64887ab79b529af3b9830
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350892B1

Reaction notes

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